1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (S)-4'-fluoro-2'-(1-methyl-1H-pyrazol-4-yl)-7'-(5-(prop-1-ynyl)pyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 336007Notes

Reaction equation

HRID 336007 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](O)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8](Br)=[CH:9][CH:10]=1.[C:23]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[N:30][CH:31]=1)#[C:24][CH3:25].[CH3:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1>>[F:20][C:14]1[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:28]4[CH:29]=[N:30][CH:31]=[C:26]([C:23]#[C:24][CH3:25])[CH:27]=4)=[CH:9][CH:10]=3)[C@@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:22]3)[C:18]=2[CH:17]=[C:16]([C:39]2[CH:38]=[N:37][N:36]([CH3:35])[CH:40]=2)[CH:15]=1

Participants

4

Reactant 3

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 58466133(S)-2-amino-7'-bromo-4'-fluoro-5H-spiro[oxazole-4,9'-xanthen]-2'-ol

Product 1

HCID 53464260(S)-4'-fluoro-2'-(1-methyl-1H-pyrazol-4-yl)-7'-(5-(prop-1-ynyl)pyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA8 above, but using (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (prepared by steps analogous to those described in Method BB40 and Example 2), 5-(prop-1-ynyl)pyridin-3-ylboronic acid, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Workup

  1. customprepared by steps analogous to

Sources & evidence

ORD record
ord-a3ec72862790418c81f6994b8f9d4868
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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